My Best Friend’s Sister

I’m out at a bar with my best friend, James when he tells me the good news: His parents are opening up their backyard pool tomorrow because the weather has been so nice, warming up early this year.The update makes me smile. I’ve spent a lot of good summers at their pool, and have a lot of good memories in their backyard. Most of my best ones have taken place at James’ house, if I’m being honest.

"Sweet!" We high five. "I’ll be there, man."

"I have to warn you though, Violet got back from college yesterday," he says. "She'll probably be there too, and I wouldn't be surprised if she invited some friends."

I roll my eyes.

"Be nice, Luke," James says.

"I'll be nice," I say. I will too, no matter how annoying I find his little sister, Violet. She's been the bane of our existence for years, constantly trying to tag along to everything, always getting into our business, and usually getting us into trouble.

James and I are like brothers, we even look alike—We’re both six-foot-one with sandy-blonde hair. The biggest difference is that James has blue eyes like the rest of his family, and I have brown. So Violet was basically a shared PITA kid-sister. Having her go away to college this past year had been great. James and I both go to school in state, so we have an apartment near campus, which is only a fifteen-minute drive from his parents’ place. Violet decided to go out of state, and I haven’t seen her since she left for school. The peace has been wonderful.

The next morning, James and I head to his parents’ in the middle of the day, already wearing our swim trunks and bringing a change of clothes for dinner. His parents have a great house, a sprawling single-family home with an awesome back porch with a picnic table and benches wrapping around the entire deck, with a big grill in between the deck and the pool. Every summer we’d spend every minute we could at the pool, usually with Violet splashing us, hitting us with wet towels, trying to tip over our floating chairs when we're resting on the water and generally making a big pain of herself. If we're lucky, she'll be out.

No such luck.

I frown when I see her for the first time, as we walk into the kitchen heading toward the back door. She's just standing there making herself a sandwich but... something's different.

"Hey James! Hey Luke!" she greets us, her voice excited, but not bubbly. Violet is not one of those girls who is constantly trying to be cute for guys. She doesn't giggle, she laughs. Loudly. Obnoxiously. She never makes her voice all high, she never squeals, and she has no problem with snakes—although she's not a huge fan of spiders. She never wears makeup and the only time I ever saw her in a dress was when her mom put up the pictures of her from prom.

That's it, that's what's different. She's wearing a sundress. It shows off her breasts. I'd never noticed that she had boobs before. Really big ones, actually. The sundress is more revealing than anything I've ever seen her in.

James elbows me and I drag my eyes out of his sister's cleavage, clearing my throat. She smirks at me.

"Hey Vi," I say lamely. "Nice to see you. How was freshman year?"

"Great! I had a lot of fun, made a lot of good friends. My roommate was awesome." She takes a giant bite out of her roast beef sandwich. Violet isn't one to babble if she doesn't have anything to say.

"Sounds good," James says, smiling at her in the way that older brothers do. "We're headed out to the pool."

Swallowing her bite of sandwich, she waves her hand at us. "Yeah, yeah, I'll be out there soon."

We head outside, put our towels down on the lounge chairs, and go grab the floating chairs that we like to sit on while we're hanging out in the pool. In less than ten minutes we're both draped in them, swim trunks soaked from a quick dip, while the hot sun slowly dries us, beer bottles securely held in their cup holders on the arms of our chairs. I love this pool.

"Dude, were you checking out my sister?" James doesn't sound mad, just curious.

"No," I lie. "It’s just weird that she’s wearing a dress."

"Huh. Yeah, I guess she doesn't do that much."

I lay on my back floating with my eyes closed.

Very relaxing.

The sun is getting kinda hot, all the water has sizzled off of my skin and I slide off my chair for another quick dip, going all the way under and coming back up at the perfect moment to see Violet emerge on the deck in a string bikini, her blonde hair up in a ponytail.

Holy. Fucking. Shit.

I've never seen her wear anything but a one-piece with a t-shirt covering it. She was always super body-shy... and now that I can see what a body she's rocking, I have no idea why she was always so modest.

The light yellow of the suit compliments her sun-kissed skin perfectly, the top is made up of triangles that look like they're straining to hold in her boobs and possibly losing the fight. The tiny triangle covering her pussy clearly shows that she's got very little hair there, if any at all. Completely ignoring us, she squirts a dollop of sunscreen onto her hand and rubs it across the top part of her chest, slowly working her way down, sliding her fingers under the strings of the bikini and then under the tiny cloth triangles. I'm pretty sure that if she turned to the side, I'd be able to see her nipples.

"Holy shit, Vi!" James shouts.

I jump. Violet jumps and her boobs bobble, threatening to spill out of the bikini top. Christ.

"What the hell are you wearing? Or should I say not wearing?"

I turn to see James glaring at her, sitting straight up on his floating chair, and fortunately ignoring me. I shift my trunks to help hide the wood that I'm sporting.

Vi's voice floats from behind me. "Oh grow up, James, I'm wearing a bikini."

"That is not a bikini! That's like... a couple pieces of Kleenex that someone tied together with strings. That should be fucking illegal. You can't walk around here wearing that in front of your family!"

I sink down into the pool up to my neck and turn my head to check out the Kleenex suit again. Violet is rolling her eyes, rubbing sunscreen into her soft stomach.

"I'm eighteen, asshole. I can do whatever I want."

James snarls. "I'm calling Mom."

"Go right ahead," she says calmly as he wades through the water, up the stairs that lead into the pool and past her into the house.

I close my eyes, because almost as soon as he's gone she starts rubbing sunscreen around her bikini bottom and her fingers trail under the fabric there too. Violet's like my little sister, not to mention that she is my best friend's little sister, and I should not be getting hard from looking at her. Period.

Two small splashes to my left make me open my eyes again. Violet is sitting on the edge of the pool, her feet dangling in the water, leaning back on her hands with her spread-apart legs. My gaze immediately zeroes in on her crotch where the yellow cloth of her bikini is barely covering her pussy lips. The puffy flesh is pushing outward against it and has almost broken free. I'm very glad that I'm in the water up to my neck because I seem to have broken out in a sweat.

"You like my bikini, don't you Luke?" She kicks her leg up at me, splashing me with water.

"It's uh... it's a little revealing, Vi." I temporize.

She pouts at me. Since when does Violet pout?

"But you like it right? It looks good?" She sits up straight, her breasts wobbling on her chest and spreads her thighs a little wider. Any more and that suit is going to split her lips.

"It's... I mean, it's whatever, Vi. I think James is right, you shouldn't be wearing something like that."

Rejection, sharp and painful shoots across her face and she actually tears up. Her legs close immediately and she hunches in on herself. I suddenly realize that she's not as confident as she seems. She was looking for a little validation—after finally getting up the nerve to wear something sexy—and I just stomped all over that.

"Oh shit... Look Vi, it looks good, okay?"

"You're just saying that," she says softly, her voice choked like she's trying to hold back emotion.

"No, seriously Violet, look…" I take a deep breath. I'm going to tell her the truth and hope that she doesn't run away from me disgusted, or worse, turn me in to James or her parents. "It's freaking hot. I'm sporting wood over here and that's uncomfortable for me ‘cause you're like my little sister."

She looks up at me with surprise, her shoulders straightening. "You've got a hard-on?"

Christ.

"Yes," I say through gritted teeth. "Don't worry though, it'll go down eventually."

Her eyes narrow. "I don't believe you."

And with that she jumps in the water. What the…?

Violet's head comes up, her blonde hair darker when wet, water clinging to her eyelashes as she blinks at me. She smiles as she comes toward me.

"What are you doing Vi?" I back away.

"I don't believe you," she challenges. "Come here and prove it."

"Vi... That is so wrong, I can't do that. You're only eighteen." I back up fast.

She rolls her eyes. "That makes me legal, dumbass."

“And still too young,” I counter.

“Yeah, cause you’re so old at twenty-one, Grandpa.”

Somehow, she's gotten me cornered at one end of the pool. My wood is starting to fade, thank god. Then she stands, water dripping off of her gorgeous mounds; the pale yellow of her bathing suit has gone nearly opaque now that it's wet and I can clearly see the outline of her hard nipples. Wood is back. Raging wood.

"Stand up," she orders. "The water's only three feet here, I'll be able to see if you're telling the truth."

"I can't."

"Stand up or let me feel it. Those are your options."

"Come on Vi..."

"Five... four... three..."

I stand before she can come at me. I know she will. We've all played around in this pool enough that I know she's just as good at water-wrestling as any guy, and if I have to grapple with her while she's wet and almost naked who knows what will come popping out. And if James comes out here and sees me touching his sister, I might very well be courting death.

Violet's eyes get big. "Wow," she mutters. "Go Luke."

"Thanks," I say dryly, sinking back down. I can't believe she made me freaking blush. "Now can you please go put on some clothes before your brother comes out here and kicks my ass?"

Violet laughs. "Only because you asked nicely."

To add insult to injury, she blows a kiss at me before stepping out of the pool. The back of her suit is just as hot as the front, her butt cheeks are hanging halfway out and the dampness of the fabric makes it cling to her crack.

She turns her head over her shoulder and catches me staring at her ass. I duck my head as she laughs, a happily triumphant sound.

“Will you come to my birthday party next Saturday?” she asks sweetly.

“Sure, sure.”

Watching her walk away does absolutely nothing to help my erection situation. Blue balls, here I come. I wish I could jerk off, but I’m too afraid of James coming out and catching me.

I walk around in the cool water thinking about old women, baseball, James’ fist pounding me into the ground…

When he finally returns, I’m back in my chair, lounging, the situation thankfully walked off.

“So what’d your mom say?”

He groans. “She bought the suit for Vi, if you can believe that. Thinks it’s great that Violet’s finally getting a better body image.”

Remembering how Violet had taken my comments, I could kind of understand that, but wow was that a racy bikini to buy your daughter.

“Well she went back inside, for now.”

“Thank god.”

“Don’t be too down on her man, she really does have bad body image.”

James looks at me like I’m crazy.

“What? She’s like my sister, I don’t want her to feel like shit about herself even if she does annoy the crap out of me.”

“Yeah, I guess you’re right,” he mutters. He keeps glancing at me though, like he’s trying to figure out what’s going on in my head. But I’ll be damned if I let him keep making Violet feel like she doesn’t look amazing, because she does and she should know that.

Two days later James and I are back at the pool and trying to ignore Violet as she tans herself. Today’s bikini is slightly more substantial, although that’s probably because her parents are home and her dad is grilling dinner. I’m doing my best not to think about all the skin that was revealed the other day.

Dinner is… awkward. Violet is sitting next to me and her lower leg keeps brushing against mine which is extremely distracting. As is the fact that she’s sitting next to me in her bikini.

“It’s so nice to have you over here for dinner, Luke,” James’ Mom says brightly. “We don’t see enough of you these days. Do you have a special lady that you’re spending all your time with?”

“No,” I reply, quickly swallowing my mouthful of hamburger. His mom insists on good manners at the table. “I was working night shifts for my Dad during school. I’ll be around more often now that summer’s here.”

“What do you do?” Violet asks.

“I’m training to be a locksmith, at least during the night shifts. Now that I’ll be doing daytime stuff, he’ll probably keep me in the office so that I can learn that side of things.”

“Are you going to take over his business one day?” She seems honestly interested.

I shrug. “Maybe. I don’t think he expects me to, but he wants me to be prepared if I do. And either way, both are good training for the real world.”

“I start my internship next week,” James cuts in. “Don’t let Luke get all the credit for forward thinking.”

We grin at each other. With the job market in the crapper the way it is, we both want to have as much experience under our belts as possible for when we graduate next year.

“Good,” James’ dad booms. “You boys are smart. You’re going to go places.”

“Thanks Mr. Potts,” I say before digging back into my food.

Violet’s foot slides up my calf and I jerk my leg away.

“You okay, Luke?” asks their mom.

“Fine, fine, just thought I felt a mosquito bite.” I reach down to scratch my leg and somehow end up touching Violet’s calf again. I can’t decide if she’s more or less annoying now than she used to be.

After dinner Mr. and Mrs. Potts take the dishes inside and Violet cleans them. I offer to dry so I can have a word with her.

“What the hell did you think you were doing out there?” I keep my voice low so no one can hear us. James and his parents are still outside, enjoying the nice night and having an after-dinner drink, but the windows and back door are open.

She smirks at me. “What’s the matter, never played footsie?”

“Not in front of anyone’s parents,” I snap back. “What’s with you?”

Vi’s blue eyes darken stormily.

“What’s with you?” she repeats back at me, her words sharp and accusing. She turns and her barely covered breasts brush my arm.

I jump back.

“Getting erections looking at your best friend’s little sister?”

“Erection, singular.”

Quick as a whip, Vi grabs one of the triangles of her top and pulls it aside, exposing a perfectly pink nipple. Very deliberately, she puts her forefinger from her opposite hand to her lips, lewdly licking the tip of her finger and then bringing it down to her nipple, circling the pink bud and teasing it to hardness.

I swallow. Hard. Twice. And shift my legs because I’ve got major wood again. I whip my eyes away, but they return of their own volition, like my free will has been subsumed by her finger and her nipple. Sweat is beading my forehead. Heavy footsteps sound on the wooden deck outside and Violet quickly covers herself again, while I adjust my erection so that it’s tucked into the band of my swimsuit and not as noticeable.

The look she gives me is very recognizable; she’s saying “I told you so” with her eyes. Somehow, now it’s cute instead of infuriating. Well, maybe it’s a little infuriating.

“Thanks for doing the dishes kids,” Mr. Potts says in his booming voice as he walks past us through the kitchen. “I’m off to bed.”

Violet trots over to him, giving me a view of her delicious backside as she gives him a kiss on the cheek. “Night, Daddy.”

Mr. Potts works early in the morning so he always goes to bed early, and I know Mrs. Potts will be following him soon. She likes to try and keep on the same schedule as him.

Violet, James and I end up rewatching Scream and drinking. Well, James and I drink. He won’t let Vi, although I see her sneak a couple sips of his beer when he goes to the bathroom. A few sips isn’t going to hurt her, so I don’t say anything. James must have either had more to drink than I thought while he was sitting out with his parents or was just really tired for some reason, because by the end of the movie he’s passed out on the couch.

“Well shit,” I say, looking at his passed-out bulk.

Vi glances at him and shrugs.

“Do you want help getting him to the car?” she asks.

“Nah, I’ll let him sleep for a bit and watch something else before I wake him up and drive home. It’s not even that late yet.”

“Yeah, I’m not in the mood to watch anything. I think I’ll go read before bed.”

“Okay,” I say, relieved that she’s back to being normal Vi.

I’m looking over the DVD shelves at the options when I hear a small moan down the hall. It has to be coming from Vi’s room; her parents’ room is upstairs. Another moan follows, this one a little louder. The legend of Bluebeard floats through my head, but that soft moaning is drawing me like a siren’s call. It sounds… erotic.

The door to Violet’s room is slightly open, just a crack, and the light is a small sliver into the dark hallway. I peek in and get a direct view into her wide-open pink pussy. I stifle my gasp, my hand covering the erection that has quickly sprung up. She’s on her back on her bed completely naked, sun-kissed legs parted and knees raised, the fingers of one hand buried in her pussy, the other squeezing her breast and pinching one hard nipple. I rub my cock as I watch her fingers sliding in and out of that glorious wetness, disappearing into her body and emerging covered in slick juices. Holy fuck. I should not be watching this… but I can’t look away.

I stick my hand into my swim trunks instead, fisting my cock as I watch her masturbate. I’m going to regret this later, I know I am, because I will never be able to get this image out of my mind and how can I ever look at her again after this?

Then she turns her head away, reaching out with the hand that had formerly been on her breast, her other hand still playing with her pussy, two of her fingers buried between her folds, and grabs a dildo that I hadn’t noticed before—no surprise there—off the end table next to the bed. As I watch in disbelief, she starts licking the dong and then pushes it all the way into her mouth… Fuck. She’s deep throating that seven-inch piece of rubber! Biting down on my lip to keep from making noise, I jerk my cock harder, imagining that it’s my eight inches sliding between those lips and down that throat.

As she plunges it in and out of her mouth, she starts squirming more, her knees pressing together and then opening, legs moving as if what she’s doing is turning her on incredibly.

Suddenly she flips over onto her stomach, and I am presented with the most incredible view of her heart-shaped ass, fingers buried deep in her pussy, rubbing herself raw. I have the most insane vision of myself leaping through the door and replacing those fingers with my dick before she can turn around and stop me. Then her fingers leave her pussy and I almost groan with disappointment, but she isn’t done.

Picking up a small bottle that had apparently been next to the dong, she does something that I can’t see and then her fingers are back between her legs, rubbing against her pussy and I’m privileged to see those digits actually part her sweet lips and slide into the wet hole. As that is happening, her other arm is coming around her ass, and it takes me a moment to even notice that she’s holding the dildo in that hand. Her face is buried in her pillows, ass high in the air, both hands behind her.

When she presses the head of the rubber dick against her asshole, I nearly lose it. That tiny, crinkled hole stretches and opens for the thick invader, and it’s the hottest thing I’ve ever seen in my life to that point. Her moaning intensifies as she begins working the dong in and out of her ass, her fingers still busy in her pussy.

Sweet Jesus, Violet has grown up with a vengeance!

I pump my cock automatically, barely paying attention to my own masturbation because I’m so involved in watching Violet’s incredible display of erotic depravity. The entire length of the toy is fully inserted into her grasping ass much faster than I would have thought possible, and then she begins to fuck herself with it. Not masturbate, not play with herself, not pleasure herself… She fucks her ass with that dong, bucking her hips and pushing back hard as she slams it in and out of her ass.

The sexy moans coming out of her throat suddenly start to form words as they increase in intensity and the movement in her ass and pussy gets faster.

“Oooooohhh fuck, Ooooh fuck, that feels so good! Oh god yes… Fuck me, fuck me please! Oh Luke, fuck my virgin ass!”

Cum spurts all over my hand and in the inside of my trunks as she says my name, pretending it’s my dick that is relentlessly pounding her anal cavity.Even though I’ve already orgasmed and now have a sticky mess to clean up, I can’t move away. The slippery dong slams into her over and over and I can see her forcing another finger into her pussy as she bucks and shudders. Her ass cheeks bounce as they clench, juices spilling from her cleft and down her thighs. Goddamn, she’s really creaming herself.

I watch the whole show. All the way to the end as she slumps and then moans, slowly sliding the dong in and out of her ass a few more times as her fingers slip out of her pussy and gently stroke the folds.

And then I hightail it out of there, rushing to the bathroom to clean myself off as best I can before returning to the family room and putting West Wing in the DVD player, hastily skipping it to the middle of an episode. Just in case.

My precautions are well worth it when, about ten minutes later, Violet comes into the room wearing a pair of pajama pants and a tank top. I don’t think she’s wearing a bra, but it’s hard to tell with the lights off.

“Sup?” I ask, feigning disinterest in her presence. My heart is still pounding, and my brain keeps playing the scene on repeat.

“Couldn’t sleep,” she says mildly.

And then we sit there and watch West Wing, her pretending that she hadn’t just violated her own ass while screaming my name and me pretending I hadn’t just watched her do it.

Because what else could we do?

I don’t go back to the Potts’ house until Wednesday afternoon when James drags my reluctant self back there. I have to go because I can’t make an excuse that won’t sound lame, and I can’t admit the real reason is his sister. I don’t know what to do about Violet. I’ve jerked off several times thinking about her sweet ass. In fact, I was finding it hard to think about anything else when I was jerking off.

It's getting harder and harder to remember what a brat Violet had been growing up as my focus turns to how much she has grown up recently. And what my cock wants to do to her grown-up body.

Not only is Violet out at the pool when we get there, but she’s wearing the pale-yellow bathing suit again. Lying on her stomach on one of the lounge chairs, she has her top untied and the bottom wedged between her butt cheeks like a thong. Her blonde hair is spread out next to her head, long and silky-looking.

“Holy crap!” James yells as soon as he gets out on the deck and has a good look at Violet’s makeshift thong. She jumps, and I get a wonderful glimpse of breast before she remembers that she her top isn’t tied, and lays down flat again.

“What the hell, James?” she snaps.

“What is it with you and not wearing any clothes?”

Violet rolls her eyes. “It’s called getting a tan, asshole.”

“Well cover your ass, because neither of us need to see it.”

I look at the ground.

“Whatever,” I hear her say, drawling out the word.

“I’m gonna go grab us some beer,” I stutter out, then turn on my heel, heading back into the house. I can hear the two of them still squabbling while I’m grabbing the beer from the fridge. I’m going to need booze to get through today, I can already tell.

By the time I get back out there, Violet is as decently covered as her skimpy bathing suit will allow and lying on her back. James is obviously trying to ignore the fact that his sister’s boobs are practically flopping out of the tiny covering. I do my best to follow his example, but I know my gaze keeps sliding over to her sexy body. Fortunately, James doesn’t seem to notice. He’s so embarrassed by Violet’s behavior that he can’t look at me either, probably assuming that I’m just as embarrassed.

Which I am, but for a completely different reason.

“Sorry dude,” he mutters as I hand him a beer.

“It’s cool man,” I say back, quiet enough that Violet can’t hear me. “She’s just doing it ‘cause she knows it bugs you. Don’t pay attention and she’ll stop.” I’m not entirely sure that’s true after what I saw Saturday night, but my boy obviously needs some reassuring. Plus, I’m pretty sure that no matter what he says, it’s not going to affect Violet’s behavior.

He groans. “I know, I know. It’s just… She’s not supposed to be dressing like that. Ever. She’s my little sister. How the hell am I supposed to deal with this?”

“By recognizing that I grew up, asshole.” Violet’s voice is loud, letting us know that she can hear what James is saying, at the very least.

James curses and takes a long pull on the beer. Seems like an appropriate response.

By 4 pm James has passed out drunk in one of the lounge chairs. Two hours before Mr. and Mrs. Potts will be home.

Violet eyes her brother.

“James.” She pokes him. “James.” The second poke is a little harder. “Jamie.”

He hates that nickname. This time she shakes him and receives nothing back but a snore.

Violet snorts derisively.

“It’s a good thing I didn’t start wearing bikinis until now,” she comments. “How could he have handled it without the booze?” She rolls her eyes again.

I shrug, treading water in the pool. I’d spent most of the afternoon there, hiding on my on-again, off-again erection.“It’s hard seeing your little sister grow up.”

“You don’t seem to mind.”

“I’m not actually your brother.”

“Oh, I know,” she murmurs thoughtfully, half under her breath.

My cock twitches. Obviously, she knows I’m not her brother. She’d been screaming my name while fucking her own ass a few nights ago.

“Hey, can I show you something? It’s for my party on Saturday.”

“Yeah, sure,” I say.

Violet hops up from her lounge chair, breasts bobbling and threatening to spill out of her bikini, as usual. I’m almost getting used to the sight, although I never stop hoping that they’ll fulfill their teasing promise.

“It’s in my room, come on.”

“Can’t you bring it out here?”

“Nope.”

“Aw, come on Violet.”

She pouts prettily at me. “You said you’d come look at it.”

I groan. Fortunately, my dick is only at half-mast at the moment, so I slog through the water and climb up the stairs to the pool deck. Smiling cheerfully now that I’m doing what she wanted, Violet leads the way back to her room on the first floor. It looks exactly the same as it had a few nights ago, except that she isn’t on the bed with a…

I wrench my thoughts back to the present before I can stiffen beneath my trunks any further. Fortunately, now that I’m out of the water and in an air-conditioned house, the wet fabric is cold and helping to inhibit my new reaction to being in close proximity to Violet.

“So what did you want to show me?”

“This.”

My jaw drops as Violet turns and her bikini bottoms fall to the floor. Her delicious ass looks even better up close. I close my eyes immediately.

“Violet!”

Her response is a soft chuckle, and then suddenly she’s pushing up against me, all warm and soft and naked…

My eyes pop open. How did she get her top off that fast?

“I thought… you said… party…” I’m stammering, stuttering, making no sense whatsoever.

“I wanted to show you what I’d like for my birthday present from you.” Her lips brush against mine, her big breasts pressed against my chest. I hold my hands in the air like she’s pointing a gun at me, not sure what else I can do with them that is acceptable.

“What?” The word comes out in an excited croak.

“I want you to take my anal virginity,” she says, leaning forward and biting my earlobe.

Instant. Wood.

My brain might be thinking about how bad James is going to kill me, possibly while taking turns with his parents, but my cock has other priorities and right now it’s filled to the brim, and ready and raring to go.

I let all my breath out as Violet’s lips travel down my neck.

“I can’t do that Vi. I mean, we can’t do that… I mean… Crap, can you cut that out, I can’t think!”

“I don’t want you to think,” she says silkily. Her hands massage my shoulders, her hard nipples rubbing against my chest. Teeth nip at my collarbone. I groan. This girl is wearing down my resistance like a microwave melts butter.

“Your brother will kill me.”

“He doesn’t have to know.”

“Your parents will kill me.”

“They don’t have to know either.”

“Why me?”

“I’ve had a crush on you for forever, but you never really saw me. This past year I had a great roommate, and she helped me plan this. I’ve been thinking about nothing else all year.”

I groan again as she rubs against me.

“Have you ever been with another guy?”

“A couple times. I haven’t had a lot of sex, but I still saved something special for you.”

The idea that she was saving her last cherry for me is just so wrong… How could I possibly be worthy of a gift like that? I’d considered her a nuisance for years and here she is, wanting me to do something wonderfully perverse because it would be special. There’s no way I deserve this.

“I don’t deserve this.” I blurt out the thought repeating over and over in my head.

“No, you don’t,” she replies calmly. “But I do deserve what I want, and what I want is you in my ass. Right here. Right now. I was going to wait till my birthday party but I’m afraid there won‘t be an opportunity, so I’m taking advantage of the fact that my parents aren’t home right now and James is passed out and not waking up any time soon.”

Her logic is flawless. I didn’t deserve her anal virginity, but she definitely deserves to be able to give it to whoever she wants, and she wants me… for whatever ungodly reason. I should just stop protesting and thank all my lucky stars.

“What if we don’t have any chemistry?”

“Well we can always find out right now.” There is a purr in her voice that hadn’t been there before.“But I don’t think it will be a problem.”

Stepping away from me, she lets me get the full view again as she grabs one of my hands and begins pulling me to the bed. Her boobs sway back and forth. Her nipples are pink and perfect and hard, and the grip of her hand is completely merciless. I take one unwilling step after another.

“What are we going to do?”

Violet smiles at me, her lashes fluttering over her eager eyes.

“You’re going to eat me out and finger my ass until I come. Then I’m going to get on all fours and you’re going to fuck my ass until I come again. You don’t have to come in my ass if you don’t want to… but I’m betting that I get to plug my ass with a load full of your spunk before we leave this room. That’s what I want from you for my birthday.”

Well, that sounds fair.

That thought lets me know that my cock has taken over and started running the show. On the other hand, if this is what she really wants—and the show she put on the other night seems to indicate that—then who am I to deny her?

I do have one question though.

“Did you know that I saw you masturbating?”

Violet laughs as she pulls me on top of her naked body. The feeling of her skin on mine undoes the last of my defenses. I’m not reluctant at all now. My brain has gone past thinking about the consequences. I have two handfuls of sweet breast flesh and an eager girl wriggling beneath me.

On top of that, I love anal sex and it’s not something that’s often offered up. Having an attractive woman seducing me into taking her in the butt, rather than me having to seduce her into it, is quite the turn-around and not one I’m immune to.

“Of course, silly. Why do you think I left my door cracked and moaned so loudly? I knew the second you started peeking.”

And then she pulls me down onto her hot little mouth.

Violet sucks me in, her lips parting and her tongue questing. Beneath my palms her nipples harden, and even though my suit is still wet, she grinds her body against me eagerly. Her hands untie the laces at the waistband of my suit. Our combined efforts get the soggy thing off my hips and onto the floor.

Skin underneath a wet bathing suit is always cold when it comes off, but Violet is so determined that she wastes no time rubbing herself against me, thighs wrapping around me, warming me up with her body as we make out. My cock is rock-hard, the tip nudging against the firm globes of her ass, practically trapping itself under her body as I grind my pubis against her pussy.

How did this nuisance grow up into such a treasure?

I want to make this good for her, to treat her right. I begin by kissing down her body, my hands moving from her breasts to her ass as my lips move from her mouth to her nipples. She curves her body around mine, her lips latching onto my earlobe as I suckle at her breast, and she nibbles my sensitive skin. The sensation goes straight to my balls, my cock bouncing against her delicious bottom, caught between her ass and the bed. My hands grip her cheeks tightly, pulling them apart as my cock slides up and down her ass crack.

Violet reaches out and grabs her bottle of lube off of the bedside table.

“Here… Lube up those fingers and put them in my ass. I want to feel you inside of me.”

Well, I’m not one to refuse a lady, even if her request is as unladylike as it gets. I kiss down her stomach. Her nipples are hard and dark pink from my attentions as I coat two of my fingers with lube. Violet’s legs spread wide as my mouth approaches her pussy, the blonde strip of hair leading me straight to her tender pink lips. As my tongue flicks at her clit, which is engorged and standing at attention, I press my slick fingers against her crinkled asshole.

It opens up easily, eagerly and Violet moans as I push into her body. Her knees bend, raising her lower body up off the bed as I start to finger-fuck her backside. Although she’d obviously been preparing it for a while, her ass is tight as fuck around my fingers, gripping them as they push back and forth inside of her. Her pussy tastes like heaven. Sweet, musky, a little bit like freshly cut cedarwood smells. I know that sounds weird, but it’s true and it’s wonderful.

“Oh Luke.” She starts moaning, humping her hips against my face and leaking pussy juices copiously. She’s so wet that I’m not sure I really need lube. The sweetness from her body is leaking down into her ass crack and coating my fingers, giving them extra wetness every time I pull partially out of her tight hole.

I end up moving my mouth down and licking around her anus.

She practically levitates off of the bed.

“Oh my god, Luke!” She plants her feet on the bed and pushes her lower body up, giving me more access. “Do that again! Oh my god… You have no idea how amazing that feels… Oh fuck!”

She likes it so much that instead of returning to her pussy, I just keep licking around her asshole as I use my other hand to start rubbing her clit. That really makes her hole clench down as she convulses with pleasure.

“Oh, Luke!” It’s just like when I’d been watching her masturbate… only a million times better. “Oh, Luke, I’m coming! Oh, fuck Luke, I’m coming!”

Violet is damn noisy as she squeals and yells and comes beautifully. I lick the juices off of her ass as they run down her crack. It’s a good thing she hadn’t waited for her party, there’s no way we would have been able to do this without getting caught. I make my way back up to her pussy, drinking up her sweet juices as her body starts to relax and her hips slow their movements. Her butt sinks back down onto the bed.

“Oh Luke…” She lets out a long breath. “That was the best orgasm of my life.”

I slide my fingers in and out of her tight ass.

“Do you still want to do the second part of your present?” I ask hopefully.

Her present. Ha! Feels more like my birthday at the moment. My birthday combined with Christmas.

Violet laughs. “Hell yes. Get those fingers out so I can turn over and then I want you to pop my butt cherry for real. And don’t be gentle. I’ve been getting myself ready for weeks. I want it to hurt a little bit, but I’m pretty sure I’ll be able to handle whatever you give me.”

I give her a few more thrusts of my fingers, making her moan with aroused surprise, then pull them out.

“I’ll probably be gentle at first,” I say, “but if you seem okay, I promise I’ll let the gentleman thing go and ride your ass hard.”

Violet shivers with lust, her eyes alight with anticipation. I had no idea she was this wild. Considering we practically grew up together, I thought I knew everything about her. Now I’m wondering what else I was wrong about.

Other than the teasing, since she’s been home again, I’ve enjoyed being around her. She’s a lot more chill and a lot less annoying. And I don’t actually mind the teasing.

My brain cuts its thought patterns as Violet turns over and gets up on her hands and knees, looking over her shoulder at me.

“Fuck my ass, Luke.” Her gaze is direct, hungry. “I want to feel your cock in my ass. I want you to pop my cherry and shoot your cum deep in my asshole.”

Roger, Houston, we are prepared for lift-off.

I put a generous amount of lube on my dick and line it up with her crinkled hole. Despite the fact that I was roughly sawing two fingers back and forth inside of it just a few minutes ago, it doesn’t look nearly big enough to take any kind of penetration. I place the head of my cock against her ass and push. It flowers, blossoms, spreads with eagerness as the wrinkles in her anus smooth out and her body opens to admit my raging erection.

“Fuuuuuuuuuck,” I moan. Pushing the head of my cock into the tightest gripping vice it’s ever felt is fucking heaven. Violet is already moaning, pushing back and trying to shove more of me into her. “Slow down, Vi.”

Her hole clenches around me, and I moan again as I push farther in. She shoves back and buries me into her hot channel, letting out a sharp yelp. I grab her hips and hold her in place.

“Dammit Vi, I told you to slow down. I don’t want to hurt you.” Her ass ripples around me and it’s a struggle to hold still.

“I didn’t think it would hurt that much,” she says in a small voice. “Just give me a second.” Her breathing is fast, her ass squeezing and constricting, massaging my cock with its constant movement.

She’s tight, hot… It feels amazing. Perfect. I want to ram back and forth like she originally asked me to, but I wait. It feels like forever.

Tired of waiting, and figuring she’ll let me know if it hurts, I start to drag my cock back out of her.

“Finally,” Violet says.

I stop.

“I thought you told me to give you a second.”

“That was way more than a second.”

“I thought you’d tell me when it was okay.”

“You were wrong.”

Violet looks over her shoulder at me again, the “brat look” on her face. The look she always gave me when she was doing something to deliberately get under my skin. Apparently, she hasn’t changed as much as I thought. Of course, now I find it cute.

“Brat,” I say, slamming my cock into her.

She whips her head back around, moaning as I start a steady thrusting in and out of her back door.

The feeling of being inside of her, of taking her anal virginity… This is exactly what I was picturing as I masturbated outside of her door a few nights ago. Being behind her, on my knees and fucking her beautiful ass. I run my hands over the firm mounds over and over again, squeezing and caressing them, then wrapping my fingers around her hips and using them to pull her back against me.

Riding Violet is like riding a bronco. She is just as into getting her ass fucked as I am into fucking her ass. Eventually I give up being remotely gentle and just start to plow into her, as rough and hard as I want.

Violet goes wild. Her ass tightens around my cock, clamping down, trying to hold me in place as I ram in and out of her tight hole. It’s slick, silky, and wonderfully forbidden. Not only am I fucking a girl in the ass… I’m anally deflowering my best friend’s sister, a girl I’ve grown up with and practically thought of as family.

And her ass is amazing. It feels like heaven around my cock.

The sensation of her ring constantly squeezing as it tries to control the motion of my thrusts is intensely pleasurable. She reaches down and starts rubbing her pussy, all of her weight on her knees and one forearm.

I can feel her start to quake beneath me. The convulsions in her ass are getting tighter, and I can tell from the changed bucking of her body that something is happening deep in her core. The way she moves becomes sinuous, undulating in front of me as her ass bounces up and down.

“Oh Luke…” She starts moaning my name and I know she must be about to orgasm. “Oh fuck, I’m coming! Luke… I’m coming!”

She squeals and jerks beneath me, her arms giving out as my body slams into hers. I can feel every muscle in her back quiver with release as she creams herself, the hand she’d been masturbating with trapped underneath her body.

My cock is wedged deep in her ass, clenched between her taut buttocks, and it swells and releases. I jerk and both of us moan as I empty what feels like a gallon of cum into her deflowered asshole.

The slight thrusting movements I make as I come send her on a second, smaller wave of orgasm, and I can feel her shuddering beneath me as I fill her with my semen. The milking ring of her ass sucks every drop of cum straight from my balls.Slowly, our noises quiet and our bodies relax.

“Damn Vi.” I rest my head on the back of her shoulder. “That was amazing.”

The soft laugh she gives me does interesting things to her insides and I moan as she ripples around my half-flaccid dick. After a few moments, I carefully ease myself out of her ass and she shivers in reaction, before turning over on her back. Looking down at her contented face, it feels like I’m truly seeing her for the first time.

I lean down and give her a kiss.

On Saturday, at Violet’s birthday party, she introduces me to her friends as her boyfriend. To my surprise, James doesn’t even try to beat me to a pulp. He gets a few threats in, but they’re unnecessary. I don’t plan on doing anything other than treating his sister with the utmost respect and keeping her happy. I’m not sure that he’d consider me constantly fucking her ass as treating her with respect, but I figure keeping her happy is the more important demand he’s made of me.